Methanol → (2S)-2-(benzylamino)-3-{[tert-butyl(dimethyl)silyl]oxy}propan-1-ol

HRID 629693노트

반응식

HRID 629693 반응식
[CH2:1]([NH:8][C@@H:9]([C:19](OC)=[O:20])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[BH4-].CO>C1COCC1>[CH2:1]([NH:8][C@H:9]([CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:13])[CH3:14])[CH2:19][OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 15456533methyl N-benzyl-O-[tert-butyl(dimethyl)silyl]-D-serinate

생성물 1

HCID 11770896(2S)-2-(benzylamino)-3-{[tert-butyl(dimethyl)silyl]oxy}propan-1-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To methyl N-benzyl-O-[tert-butyl(dimethyl)silyl]-D-serinate (1 eq.) in THF (0.4 M) at rt were added 2M LiBH4 in THF (1.2 eq.) and MeOH (1.2 eq). The mixture was stirred at rt for 16 hrs and quenched by the slow addition of saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was used as such for the next step.

후처리

  1. customquenched by the slow addition of saturated aqueous NH4Cl
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f59fc9fae4d34d4ebe4c25a1d46e94bb
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315475B2

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