Water → 6-(Benzyloxy)-7-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 1944215ノート

反応式

HRID 1944215 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[C:15]([CH3:21])=[N:14][CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.[Cl-].[Na+]>CCO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[CH:15]([CH3:21])[NH:14][CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 409929HCID 409929、化合物HCID 4311764Sodium borohydride

生成物 1

HCID 6226266-(Benzyloxy)-7-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline収率 63%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 249 (949 mg, 3.4 mmol) in EtOH (15 ml) at 0° C. was added sodium borohydride (256 mg, 6.8 mmol) portionwise. The reaction mixture was stirred at rt for 1.5 h. Water (100 ml) was added and the aqueous layer was neutralised. The aqueous layer was saturated with sodium chloride and extracted with EtOAc (3×100 ml). The combined organic layers were washed with sat. aq. sodium hydrogen C(Ar)bonate (100 ml), dried (MgSO4) and concentrated in vacuo to afford the title compound (600 mg, 63%) a yellow oil. 1H NMR (400 MHz; DMSO-d6) 1.58 (3H, d, J=6.4 Hz, CH3CH), 2.50 (2H, s, CH2), 2.82-2.95 (2H, m, CH2), 3.76 (3H, s, OCH3), 4.42 (1H, q, J=6.4 Hz, CH3CH), 5.06 (2H, s, CH2Ph), 6.86 (1H, s, CH), 6.88 (1H, s, CH), 7.31-7.44 (5H, m, 5×CH, phenyl), 9.40 (1H, brs, NH). LC/MS (ES+) tr=0.73 min, m/z 284.13 (M++H).

後処理

  1. extractionextracted with EtOAc (3×100 ml)
  2. washThe combined organic layers were washed with sat. aq. sodium hydrogen C(Ar)bonate (100 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a32f2bf8127d471b893166a94eecfbe7
出典データセット
uspto-grants-2013_03
特許番号
US08394825B2

反応ノート

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