[(1S)-1-(t-butyldiphenylsilyloxymethyl)propyl]carbamic acid benzyl ester → (1S)-1-(t-butyldiphenylsilyloxymethyl)propylamine

HRID 891632ノート

反応式

HRID 891632 の反応式
C(OC(=O)[NH:10][C@H:11]([CH2:14][O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:12][CH3:13])C1C=CC=CC=1>CO.[Pd]>[Si:16]([O:15][CH2:14][C@@H:11]([NH2:10])[CH2:12][CH3:13])([C:29]([CH3:31])([CH3:32])[CH3:30])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

4

反応物 1

HCID 60109785[(1S)-1-(t-butyldiphenylsilyloxymethyl)propyl]carbamic acid benzyl ester

生成物 1

HCID 23598348(1S)-1-(t-butyldiphenylsilyloxymethyl)propylamine収率 88.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A solution of [(1S)-1-(t-butyldiphenylsilyloxymethyl)propyl]carbamic acid benzyl ester (3.70 g, 8.00 mmol) (obtained as described in Reference Example 34(1)) in methanol (185 ml) was subjected to catalytic hydrogenation in the presence of 10% palladium on charcoal (3.70 g) at room temperature for 4 hours. After checking the completion of the reaction, the reaction mixture was filtered in order to remove the catalyst and the filtrate concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using methylene chloride:methanol (9:1) as the eluant to afford (1S)-1-(t-butyldiphenylsilyloxymethyl)propylamine (2.32 g, yield 88%) as a colorless oil.

後処理

  1. customthe completion of the reaction
  2. filtrationthe reaction mixture was filtered in order
  3. customto remove the catalyst
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-fca0f4af0c1846d7bf069eb9c05244f6
出典データセット
uspto-grants-2006_02
特許番号
US07001897B2

反応ノート

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