Sodium borohydride → HCID 68015080, compound

HRID 1913030Notes

Reaction equation

HRID 1913030 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]([Cl:39])=[C:35]([CH2:40][C:41]3[CH:42]=[CH:43][C:44]4[O:48][CH2:47][CH2:46][C:45]=4[CH:49]=3)[CH:34]=2)([O:31][CH3:32])[O:11][C@:10]1([CH2:52][OH:53])[CH:50]=[O:51])[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:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@@:12]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]3[CH:42]=[CH:43][C:44]4[O:48][CH2:47][CH2:46][C:45]=4[CH:49]=3)[CH:34]=2)([O:31][CH3:32])[O:11][C:10]1([CH2:52][OH:53])[CH2:50][OH:51])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 86685134HCID 86685134, compound

Product 1

HCID 68015080HCID 68015080, compoundYield 28.8%

Procedure

(2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-carbaldehyde 5j (4.36 g, 5.93 mmol) was dissolved in 50 mL of mixed solution (THF and MeOH, v:v=1:1), followed by addition of sodium borohydride (0.45 g, 11.9 mmol). The reaction mixture was stirred for 30 minutes. Thereafter, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system D to obtain the title compound [(3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol 5k (1.26 g, white solid), yield: 28.8%. 1H NMR (400 MHz, CD3OD): δ 7.53 (dd, 1H), 7.44 (d, 1H), 7.35 (d, 1H), 7.31-7.26 (m, 5H), 7.25-7.18 (m, 8H), 7.04-7.02 (m, 2H), 6.90 (s, 1H), 6.80 (d, 1H), 6.54 (d, 1H), 4.90-4.79 (m, 4H), 4.73 (d, 1H), 4.54 (d, 1H), 4.46-4.41 (m, 2H), 4.20 (t, 1H), 4.10-4.00 (m, 5H), 3.88 (dd, 2H), 3.74 (d, 1H), 3.15 (s, 3H), 3.06-3.00 (m, 2H).

Workup

  1. concentrationThereafter, the reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel chromatography with elution system D

Sources & evidence

ORD record
ord-f18d0f58840046cab97bb948c96acdad
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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