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

HRID 1944215노트

반응식

HRID 1944215 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 409929HCID 409929, 화합물HCID 4311764Sodium borohydride

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a32f2bf8127d471b893166a94eecfbe7
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394825B2

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