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(2S)-2-amino-2-(4-chlorophenyl)acetic acid → (S)-2-Amino-2-(4-chlorophenyl)ethanol

HRID 555705
Notes
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Reaction equation

HRID 555705 reaction equation
[CH:1]1[C:6]([C@H:7]([NH2:11])[C:8](O)=[O:9])=[CH:5][CH:4]=[C:3]([Cl:12])[CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:11][C@@H:7]([C:6]1[CH:5]=[CH:4][C:3]([Cl:12])=[CH:2][CH:1]=1)[CH2:8][OH:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 738019(2S)-2-amino-2-(4-chlorophenyl)acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 42579783(S)-2-Amino-2-(4-chlorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of L-4-chloro-phenylglycine (1.74 g, 9.37 mmol) and LAH (712 mg, 18.75 mmol) in THF (40 mL) is refluxed for 1.5 h. After completion, the reaction mixture is quenched by Na2SO4.10H2O and the product is isolated by filtration with Celite, washed with THF and dried under reduced pressure to give the title compound as oil; HPLC: AtRet=1.46 min; 1HNMR (DMSO-d6) 7.35 (d, 2H), 7.30 (d, 2H), 4.80 (bs, 1H), 3.85-3.80 (m, 1H), 3.45-3.20 (m, 2H), 1.85 (bs, 2H).

Workup

  1. temperatureis refluxed for 1.5 h
  2. customAfter completion, the reaction mixture is quenched by Na2SO4.10H2O
  3. customthe product is isolated by filtration with Celite
  4. washwashed with THF
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-906babafbc5a44abb927d546ccb97ef5
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08053457B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes