Sodium borohydride → HCID 86685162, compound

HRID 1913065Notes

Reaction equation

HRID 1913065 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@:12]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[C:35]([CH2:40][C:41]3[S:42][C:43]([C:46]4[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=4)=[CH:44][CH:45]=3)[CH:34]=2)([O:31][CH3:32])[O:11][C@:10]1([CH2:55][OH:56])[CH:53]=[O:54])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>>[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@:12]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[C:35]([CH2:40][C:41]3[S:42][C:43]([C:46]4[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=4)=[CH:44][CH:45]=3)[CH:34]=2)([O:31][CH3:32])[O:11][C:10]1([CH2:53][OH:54])[CH2:55][OH:56])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 86685161HCID 86685161, compound

Product 1

HCID 86685162HCID 86685162, compoundYield 25.8%

Procedure

(2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-carbaldehyde 91 (2.0 g, 2.1 mmol) was dissolved in 30 mL of mixed solution (THF and MeOH, v:v=1:20), followed by addition of sodium borohydride (238 mg, 6.3 mmol) in batch. The reaction mixture was stirred for 1 hour. Thereafter, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution systems B and E to obtain the title compound [(3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol 9j (420 mg, pale yellow solid), yield: 25.8%. 1H NMR (400 MHz, CD3OD): δ 7.55 (d, 2H), 7.48-7.45 (m, 3H), 7.32-7.28 (m, 5H), 7.25-7.21 (m, 9H), 7.16 (d, 2H), 7.07-7.03 (m, 3H), 6.63 (d, 1H), 4.91 (d, 1H), 4.83 (d, 1H), 4.75 (d, 1H), 4.54 (d, 1H), 4.26-4.17 (m, 2H), 4.10-4.04 (m, 5H), 3.94 (d, 1H), 3.78 (d, 1H), 3.36 (d, 1H), 3.26 (s, 3H), 2.34 (s, 3H).

Workup

  1. concentrationThereafter, the reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel chromatography with elution systems B and E

Sources & evidence

ORD record
ord-ab468f64f1f54ac19ebd5b1f4b56b2f5
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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