Triethylamine → 3-(RS)-[2-(4-Bromobenzyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-ylmethyl]-4-(SR)-phenylpyrrolidine-1-carboxylic Acid Tert-Butyl Ester

HRID 1182161ノート

反応式

HRID 1182161 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([CH:19]=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[Br:22][C:23]1[CH:40]=[CH:39][C:26]([CH2:27][N:28]2[CH2:32][CH2:31][C:30]3([CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[C:29]2=[O:38])=[CH:25][CH:24]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C(=O)(O)[O-].[Na+]>ClCCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([CH2:19][N:35]2[CH2:34][CH2:33][C:30]3([C:29](=[O:38])[N:28]([CH2:27][C:26]4[CH:25]=[CH:24][C:23]([Br:22])=[CH:40][CH:39]=4)[CH2:32][CH2:31]3)[CH2:37][CH2:36]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2724942TriacetoxyborohydrideHCID 450741072,8-Diazaspiro[4.5]decan-1-one, 2-[(4-bromophenyl)methyl]-, (Hydrochloride) (1:1)HCID 724802973-(RS)-formyl-4-(SR)-phenylpyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 673694643-(RS)-[2-(4-Bromobenzyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-ylmethyl]-4-(SR)-phenylpyrrolidine-1-carboxylic Acid Tert-Butyl Ester収率 89.3%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To 275.3 mg (1 mmol) of 3-(RS)-formyl-4-(SR)-phenylpyrrolidine-1-carboxylic acid tert-butyl ester and 359.1 mg (1 mmol) of 2-(4-bromobenzyl)-2,8-diaza-spiro[4.5]decan-1-one hydrochloride were added 20 mL of DCE and 139 μL (1 mmol) of triethylamine. The reaction mixture was agitated for 10 minutes at room temperature before adding 334 mg (1.5 mmol) of triacetoxyborohydride. After an overnight agitation, 10 mL of saturated solution of sodium bicarbonate were added and the solution was extracted with DCM. The organic layers were dried over sodium sulfate, filtered and evaporated in vacuo. The crude yellow oil was purified by flash chromatography on silica gel (DCM/methanol 0% to 2%) giving Compound 1 as a colorless solid (520 mg, 89.3%).

後処理

  1. extractionthe solution was extracted with DCM
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude yellow oil was purified by flash chromatography on silica gel (DCM/methanol 0% to 2%)

出典と根拠

ORDレコード
ord-b5d633ae83074b05bafe19ab8098a007
出典データセット
uspto-grants-2007_10
特許番号
US07288548B2

反応ノート

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