Tert-Butylamine → 2-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(tert-butylamino)cyclohexylcarbamate

HRID 2246597ノート

反応式

HRID 2246597 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]2[CH2:22][CH2:21][C:20](=O)[CH2:19][C@H:18]2[NH:24][C:25](=[O:33])[O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:13]1=[O:34])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]([NH2:39])([CH3:38])([CH3:37])[CH3:36].C([BH3-])#N.[Na+].[OH-].[Na+]>C(Cl)Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CO>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]2[CH2:22][CH2:21][C@@H:20]([NH:39][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:19][C@H:18]2[NH:24][C:25](=[O:33])[O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:31])[CH3:32])[C:13]1=[O:34])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 6385Tert-ButylamineHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 866181582-(trimethylsilyl)ethyl (1R,2S)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-oxocyclohexylcarbamate

生成物 1

HCID 866181402-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(tert-butylamino)cyclohexylcarbamate収率 83%

試薬・触媒・溶媒 3

HCID 11026Titanium isopropoxide触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-(trimethylsilyl)ethyl (1R,2S)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-oxocyclohexylcarbamate (0.550 g, 1.123 mmol) in methylene chloride (0.4 mL) was added t-butylamine (1.180 ml, 11.23 mmol) and Titanium(IV) isopropoxide (6.63 ml, 22.47 mmol). This mixture was stirred for 2 h before sodium cyanoborohydride (127 mg, 2.022 mmol) and MeOH (1 mL) were added. After 2 h, methylene chloride (50 mL) was added, followed by 1N NaOH. The mixture was filtered through Celite to remove the titanium salts. The filtrate was dried and concentrated in vacuo to give 2-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(tert-butylamino)cyclohexylcarbamate and its 5S diastereomer as a mixture (510 mg, 0.933 mmol, 83% yield). LC/MS found [M+H]+=547.31.

後処理

  1. additionwere added
  2. filtrationThe mixture was filtered through Celite
  3. customto remove the titanium salts
  4. customThe filtrate was dried
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7ec92587c0914631a5a0427e4cb359d3
出典データセット
uspto-grants-2010_03
特許番号
US07687508B2

反応ノート

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