Borane;tetrahydrofuran → (2S)-1-(1-Benzhydryl-azetidin-3-ylamino)-3-(4-benzyloxy-phenoxy)-propan-2-ol

HRID 2300208Notes

Reaction equation

HRID 2300208 reaction equation
[CH:1]([N:14]1[CH2:17][C:16](=[N:18][CH2:19][C@H:20]([OH:37])[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:25][CH:24]=2)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.O1CCCC1>O1CCCC1>[CH:1]([N:14]1[CH2:15][CH:16]([NH:18][CH2:19][C@H:20]([OH:37])[CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:27][CH:28]=2)[CH2:17]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 12044730(2S)-1-(1-Benzhydryl-azetidin-3-ylideneamino)-3-(4-benzyloxy-phenoxy)-propan-2-ol

Product 1

HCID 12044731(2S)-1-(1-Benzhydryl-azetidin-3-ylamino)-3-(4-benzyloxy-phenoxy)-propan-2-olYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S)-1-(1-Benzhydryl-azetidin-3-ylideneamino)-3-(4-benzyloxy-phenoxy)-propan-2-ol (0.49 g, 1 mmol) in tetrahydrofuran (4 ml) was added 1.2 ml of borane-tetrahydrofuran (1.0 M in THF), and the mixture was stirred at room temperature for 20 h. It was then quenched with 1.5 ml of 2 N NaOH, and the volatiles were evaporated. The aqueous solution was removed, and the residue was washed with water, and treated with 3 ml of 2 N HCL and 3 ml of methanol for 20 h. The mixture was then made alkaline with 1 N NaOH, and the methanol was evaporated. The resulting suspension was filtered, and the precipitate washed with water, and dried in vacuo to give 0.46 g of a white solid; m.p. 109-110°C.; MS (ES) m/z 495.7 (MH+); HRMS (El) Calcd. for C32H34N2O3 (M+): 494.2570, Found: 494.2561.

Workup

  1. customIt was then quenched with 1.5 ml of 2 N NaOH
  2. customthe volatiles were evaporated
  3. customThe aqueous solution was removed
  4. washthe residue was washed with water
  5. additiontreated with 3 ml of 2 N HCL and 3 ml of methanol for 20 h
  6. customthe methanol was evaporated
  7. filtrationThe resulting suspension was filtered
  8. washthe precipitate washed with water
  9. customdried in vacuo

Sources & evidence

ORD record
ord-f92279f65594405799450bba77026405
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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