Water → (S)-methyl 2-((4-hydroxycyclohexyl)amino)-2-phenylacetate

HRID 525325

反応式

HRID 525325 の反応式
[CH3:1][O:2][C:3](=[O:12])[C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[NH2:5].[OH:13][CH:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[OH:13][CH:14]1[CH2:19][CH2:18][CH:17]([NH:5][C@@H:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([O:2][CH3:1])=[O:12])[CH2:16][CH2:15]1

参加物

6

反応物 4

HCID 962WaterHCID 5437064-HydroxycyclohexanoneHCID 1201451Methyl phenylglycinate, L-HCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 89814327(S)-methyl 2-((4-hydroxycyclohexyl)amino)-2-phenylacetate収率 35%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

(S)-(+)-2-Phenylglycine methyl ester (commercially available from Sigma-Aldrich, Milwaukee, Wis., 433 g, 2.146 mol) was added to a solution of 4-hydroxycyclohexanone (245 g, 2.146 mol) in DCE (8.5 L). Sodium triacetoxyborohydride was added (910 g, 4.292 mol), and the mixture was stirred at room temperature under nitrogen for 23 hours. Water (3 L) was added to quench the reaction, and the organic layer was separated. The aqueous phase was extracted with DCM (4 L×2) and the organic layers were combined, dried, filtered and concentrated. The residue was purified by column chromatography (gradient elution with 100% DCM to DCM/MeOH=25:1) to afford (S)-methyl 2-((4-hydroxycyclohexyl)amino)-2-phenylacetate (197 g, 35%) (mixture of cis and trans). m/z (ESI) 264 (M+H)+.

後処理

  1. customto quench
  2. customthe reaction
  3. customthe organic layer was separated
  4. extractionThe aqueous phase was extracted with DCM (4 L×2)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (gradient elution with 100% DCM to DCM/MeOH=25:1)

出典と根拠

ORDレコード
ord-86b7ddc4ecfb4365b550de1dc67b1548
出典データセット
uspto-grants-2016_05
特許番号
US09340549B2

関連ノート

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