Sodium triacetoxyborohydride → (1R)-2-{[6-(But-3-ynyloxy)hexyl][(1S)-2-hydroxy-1-phenylethyl]amino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

HRID 2118178Notes

Reaction equation

HRID 2118178 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=O)[CH2:2][C:3]#[CH:4].[CH3:13][C:14]1([CH3:37])[O:19][C:18]2[CH:20]=[CH:21][C:22]([C@@H:24]([OH:36])[CH2:25][NH:26][C@@H:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:28][OH:29])=[CH:23][C:17]=2[CH2:16][O:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[CH2:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:26]([C@@H:27]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:28][OH:29])[CH2:25][C@@H:24]([C:22]1[CH:21]=[CH:20][C:18]2[O:19][C:14]([CH3:13])([CH3:37])[O:15][CH2:16][C:17]=2[CH:23]=1)[OH:36])[CH2:2][C:3]#[CH:4]

Participants

7

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 11163708(1R)-1-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-{[(1S)-2-hydroxy-1-phenylethyl]amino}ethanolHCID 218670216-(But-3-ynyloxy)hexanal

Product 1

HCID 86595261(1R)-2-{[6-(But-3-ynyloxy)hexyl][(1S)-2-hydroxy-1-phenylethyl]amino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanolYield 79%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 6-(but-3-ynyloxy)hexanal (434 mg) and (1R)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-{[(1S)-2-hydroxy-1-phenylethyl]amino}ethanol (710 mg) (WO/0196278) in chloroform (10 ml) was treated at 20° C. with sodium triacetoxyborohydride (866 mg) and stirred under nitrogen for 2 days. The mixture was diluted with ethyl acetate and aqueous sodium bicarbonate solution. The organic phase was separated and washed with sodium bicarbonate solution, brine, dried and purified on a silica Bond Elut cartridge (10 g) eluting with dichloromethane, diethyl ether and finally ethyl acetate to give the title compound (810 mg): LCMS RT=2.69 min, ES+ve m/z 496 (M+H)+.

Workup

  1. customThe organic phase was separated
  2. washwashed with sodium bicarbonate solution, brine
  3. customdried
  4. custompurified on a silica Bond Elut cartridge (10 g)
  5. washeluting with dichloromethane, diethyl ether and finally ethyl acetate

Sources & evidence

ORD record
ord-a1a1dc96728e488abc6f1eb46cc7acc2
Source dataset
uspto-grants-2008_10
Patent number
US07442836B2

Reaction notes

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