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

HRID 20795

반응식

HRID 20795 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

출처 및 근거

ORD 기록
ord-4a1f6424cb75411fb3b7839e04221e0e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745642B2

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