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rac-ethyl (1R,2S)-2-aminocyclopentane-1-carboxylate hydrochloride → cis-2-[(5-Fluoro-pyridin-2-ylmethyl)-amino]-cyclopentanecarboxylic acid ethyl ester

HRID 731246
Notes
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Reaction equation

HRID 731246 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[F:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]=O)=[N:18][CH:19]=1.C([BH3-])#N.[Na+]>C(O)C.C(O)(=O)C>[CH2:11]([O:10][C:8]([C@@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:3]1[NH:2][CH2:20][C:17]1[CH:16]=[CH:15][C:14]([F:13])=[CH:19][N:18]=1)=[O:9])[CH3:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 2725067rac-ethyl (1R,2S)-2-aminocyclopentane-1-carboxylate hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 103516975-Fluoropyridine-2-carboxaldehyde

Product 1

HCID 69063754cis-2-[(5-Fluoro-pyridin-2-ylmethyl)-amino]-cyclopentanecarboxylic acid ethyl esterYield 52.5%

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Catalyst
HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of ethyl cis-2-amino-1-cyclopentane carboxylate hydrochloride (0.250 g, 1.29 mmol) in ethanol (10 mL) was treated with 5-fluoro-pyridine-2-carbaldehyde, glacial acetic acid (10 drops), sodium cyanoborohydride (0.162 g, 2.58 mmol) and stirred for 72 h at 50° C. The reaction was extracted with ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate solution (100 mL). The organic layer was dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash column chromatography (Teledyne Isco RediSep Flash Column 10 g; 0-10% methanol in dichloromethane) to afford the desired product, cis-2-[(5-fluoro-pyridin-2-ylmethyl)-amino]-cyclopentanecarboxylic acid ethyl ester (0.179 g, 0.678 mmol, 52.5%), as a light yellow oil. LC-MS (ESI) calcd for C14H19FN2O2 266.14, found 267.2 [M+H+].

Workup

  1. extractionThe reaction was extracted with ethyl acetate (100 mL)
  2. washwashed with saturated aqueous sodium bicarbonate solution (100 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by flash column chromatography (Teledyne Isco RediSep Flash Column 10 g; 0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f94f87a9043a4661a3f06db450272fda
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07582626B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes