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

HRID 629693ノート

反応式

HRID 629693 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f59fc9fae4d34d4ebe4c25a1d46e94bb
出典データセット
uspto-grants-2016_04
特許番号
US09315475B2

反応ノート

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