(R)-(+)-N-Boc-2-piperidinecarboxylic acid
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(R)-(+)-N-Boc-2-piperidinecarboxylic acid
structure -
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CAS No:
28697-17-8
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Formula:
C11H19NO4
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Chemical Name:
(R)-(+)-N-Boc-2-piperidinecarboxylic acid
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Synonyms:
(R)-PIPERIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER;(R)-(+)-N-BOC-2-PIPERIDINECARBOXYLIC ACID;(R)-(-)-N-BOC-PIPECOLIC ACID;(R)-N-BOC-PIPERIDINE-2-CARBOXYLIC ACID;(R)-N-TERT-BUTYLOXYCARBONYL-PIPERIDINE-2-CARBOXYLIC ACID;(R)-1-N-BOC-PIPECOLINIC ACID;(R)-1-N-BOC-PIPERIDINE-2-CARBOXYLIC ACID;(R)-(+)-1-(TERT-BUTOXYCARBONYL)-2-PIPERIDINECARBOXYLIC ACID
- Categories:
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CAS No:
(R)-(+)-N-Boc-2-piperidinecarboxylic acid Basic Attributes
229.27
229.131409
DTXSID70350923
2933399090
Characteristics
66.8
1.8
White to brown Crystalline Powder
1.2±0.1 g/cm3
116-119 °C(lit.)
167.4±25.9 °C
1.496
soluble in 2ml dimethyl formamide 0.3gram.
Store at RT.
68 º (c=1 in acetic acid)
Safety Information
IRRITANT
NONH for all modes of transport
3
36/37/38
26-36
Xi
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
(R)-(+)-N-Boc-2-piperidinecarboxylic acid Use and Manufacturing
To a 1000 mL round bottom flask, 2R-piperidine carboxylic acid (8.0 g, 0.062 mol), di-tert-butyl dicarbonate (14.8 g, 0.068 mol), sodium bicarbonate (26.04 g, 0.310 mol) and methanol (400 mL) were added, and stirred at room temperature for 24 hours. Thereafter, the reaction product was subjected to vacuum distillation for removal of methanol, dissolved with water, washed 3 times with ethyl ether, adjusted to pH = 2 with saturated potassium hydrogen sulfate, and extracted 3 times with dichloromethane. The extracts were combined, washed 3 times with saturated brine, concentrated, and separated through a silica gel column (eluent: petroleum ether/ethyl acetate/acetic acid), to give 12.48 g of a white product, yield 87.8percent. [0075] To a 1000 mL round bottom flask, 2R-piperidine carboxylic acid (8.0 g, 0.062 mol), di-tert-butyl dicarbonate (14.8 g, 0.068 mol), sodium bicarbonate (26.04 g, 0.310 mol) and methanol (400 mL) were added, and stirred at room temperature for 24 hours. Thereafter, the reaction product was subjected to vacuum distillation for removal of methanol, dissolved with water, washed 3 times with ethyl ether, adjusted to pH=2 with saturated potassium hydrogen sulfate, and extracted 3 times with dichloromethane. The extracts were combined, washed 3 times with saturated brine, concentrated, and separated through a silica gel column (eluent: petroleum ether/ethyl acetate/acetic acid), to give 12.48 g of a white product, yield 87.8percent.To a suspension of (R)-piperidine-2-carboxylic acid (12.5 g, 96.8 mmol) in water (88mL) and 1, 4-dioxane (133 mL), were added di-tert-butyl dicarbonate (23.2 g, 106 mmol) andtriethylamine (13.5 mL, 96.8 mmol). The solution was stirred at room temperature for 20hours. The mixture was concentrated in vacuo, diluted with ethyl acetate (200 mL) and25 washed with 5percent aqueous HCl. The organic phase was separated, dried over anhydrousNa2S04, filtered, and concentrated to afford the compound as a white solid (18.5 g, 83percent).MS 130 (MH+- boc).
Computed Properties
Molecular Weight:229.27
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:229.13140809
Monoisotopic Mass:229.13140809
Topological Polar Surface Area:66.8
Heavy Atom Count:16
Complexity:282
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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(R)-(+)-N-Boc-2-piperidinecarboxylic acid
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