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Sodium borohydride → (+/-)1-[1-(1-Azetidinyl)cyclopentyl]-1-phenylmethanamine

HRID 20795
Notes
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Reaction equation

HRID 20795 reaction equation
[N:1]1([C:5]2([C:10]#[N:11])[CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[C:12]1([Li])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[BH4-].[Na+].NC(C1C=CC=CC=1)C1(N(C)C)CCCC1>C1COCC1.CO>[N:1]1([C:5]2([CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH2:11])[CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:2][CH2:3][CH2:4]1
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4311764Sodium borohydrideHCID 11521393{1-[Amino(phenyl)methyl]cyclopentyl}dimethylamineHCID 593477791-(1-Azetidinyl)cyclopentanecarbonitrileHCID 178506676HCID 178506676, compound

Product 1

HCID 59347827(+/-)1-[1-(1-Azetidinyl)cyclopentyl]-1-phenylmethanamineYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

The title compound (0.45 g, 47%) was prepared from 1-(1-azetidinyl)cyclopentanecarbonitrile D13 (0.60 g, 4.0 mmol), and phenyllithium in ethers (2.6 ml of a 1.7M solution; 4.4 mmol) in THF (5 ml), followed by reaction with sodium borohydride (0.456 g, 12 mmol) in methanol (5 ml) in a similar manner to that described in D2. 1H NMR (CDCl3) δ: 0.67 (1H, m), 1.06 (1H, m), 1.32 (4H, m), 1.48 (2H, m), 1.91-2.03 (4H, m), 3.24 (4H, m), 3.83 (1H, s), 7.20-7.32 (3H, m), 7.44 (2H, m).

Sources & evidence

ORD record
ord-4a1f6424cb75411fb3b7839e04221e0e
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745642B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes