Sodium borohydride → HCID 68015104, compound

HRID 1055588Notes

Reaction equation

HRID 1055588 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:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[C:43]([F:50])[C:42]=3[F:51])[CH:34]=2)([O:31][CH3:32])[O:11][C@@:10]1([CH2:54][OH:55])[CH:52]=[O:53])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[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:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[C:43]([F:50])[C:42]=3[F:51])[CH:34]=2)([O:31][CH3:32])[O:11][C:10]1([CH2:54][OH:55])[CH2:52][OH:53])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118377807HCID 118377807, compound

Product 1

HCID 68015104HCID 68015104, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2R,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl) methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-carbaldehyde 23l (3.30 g, 4.31 mmol) in methanol (60 mL) was added sodium borohydride (326 mg, 8.62 mmol) at 0° C. The mixture was warmed up to room temperature and stirred for 30 min. The reaction mixture was quenched with saturated aqueous ammonium chloride (15 mL), and then water (20 mL) was added. The mixture was extracted with ethyl acetate (30 mL×3). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 23m as yellow oil (3.41 g, 100%). This material was not further purified. The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, DMSO-d6) δ(ppm): 7.57 (m, 1H), 7.45 (m, 2H), 7.28 (m, 13H), 7.03 (m, 2H), 6.78 (t, 1H), 6.60 (t, 1H), 4.87 (s, 1H), 4.79 (m, 3H), 4.68 (d, 1H), 4.51 (d, 1H), 4.39 (s, 1H), 4.06 (m, 5H), 3.93 (t, 3H), 3.77 (m, 2H), 3.52 (d, 1H), 3.18 (d, 1H), 3.09 (s, 3H), 1.32 (t, 3H).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride (15 mL)
  2. additionwater (20 mL) was added
  3. extractionThe mixture was extracted with ethyl acetate (30 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7a6a2f4547224aa4b2c902c6c39d5635
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

Loading…