(+)-N-[{1-[bis(phenylmethyl)amino]cyclopentyl}(phenyl)methyl]-2,6-dimethylbenzamide → (+/-)-N-[(1-aminocyclopentyl)(phenyl)methyl]-2,6-dimethylbenzamide

HRID 20845노트

반응식

HRID 20845 반응식
C1(C[N:8](CC2C=CC=CC=2)[C:9]2([CH:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:15][C:16](=[O:25])[C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:24])[CH2:13][CH2:12][CH2:11][CH2:10]2)C=CC=CC=1>[Pd].[C].C(O)C>[NH2:8][C:9]1([CH:14]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[NH:15][C:16](=[O:25])[C:17]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:24])[CH2:13][CH2:12][CH2:11][CH2:10]1

참가 물질

4

반응물 1

HCID 59347832(+)-N-[{1-[bis(phenylmethyl)amino]cyclopentyl}(phenyl)methyl]-2,6-dimethylbenzamide

생성물 1

HCID 59347772(+/-)-N-[(1-aminocyclopentyl)(phenyl)methyl]-2,6-dimethylbenzamide수율 88%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 702Ethanol용매

실험 절차

The title compound (1.14 g; 71%) was prepared from the catalytic hydrogenation of (±)-N-[{1-[bis(phenylmethyl)amino]cyclopentyl}(phenyl)methyl]-2,6-dimethylbenzamide D34 (2.51 g; 5 mmol) over 10% Pd/Carbon (0.4 g) in 3 MHCl (8 ml) and ethanol (150 ml) in a similar manner to that described in D29. The ethanol was evaporated off in vacuo and the residual material was partitioned between DCM and sodium bicarbonate solution and dried (Na2SO4). The filtrate was reduced in volume by evaporation in vacuo and loaded onto an SCX cartridge. Washing with DCM, then methanol followed by elution with 1M ammonia in methanol afforded the title product (90 mg, 88%). 1H NMR (CDCl3) δ: 0.98-1.96 (10H, m). 2.23 (6H, s), 4.97 (1H, m), 7.0 (2H, m), 7.16 (1H, m), 7.22-7.41 (6H, m); Mass Spectrum (Electrospray LC/MS). Found 323 (MH+). C21H26N2O requires 322. Ret. time 1.69 min.

후처리

  1. customThe ethanol was evaporated off in vacuo
  2. customthe residual material was partitioned between DCM and sodium bicarbonate solution
  3. dry with materialdried (Na2SO4)
  4. customThe filtrate was reduced in volume by evaporation in vacuo
  5. washWashing with DCM
  6. washmethanol followed by elution with 1M ammonia in methanol

출처 및 근거

ORD 기록
ord-b1fb220a6ee241009edb0a778260bc95
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745642B2

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