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

HRID 525325

반응식

HRID 525325 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

(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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-86b7ddc4ecfb4365b550de1dc67b1548
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340549B2

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