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

HRID 20845ノート

反応式

HRID 20845 の反応式
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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b1fb220a6ee241009edb0a778260bc95
出典データセット
uspto-grants-2010_06
特許番号
US07745642B2

反応ノート

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