Sodium borohydride → HCID 131735094, compound

HRID 929204Notes

Reaction equation

HRID 929204 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:23]([O:33][C@H:34]3[C@H:38]4[O:39][CH2:40][C@@H:41]([O:42][CH2:43][CH:44]=[O:45])[C@H:37]4[O:36][CH2:35]3)=[N:22][C:7]2=[N:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1>CO>[Cl:3][C:4]1[CH:5]=[C:6]2[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:23]([O:33][C@H:34]3[C@H:38]4[O:39][CH2:40][C@@H:41]([O:42][CH2:43][CH2:44][OH:45])[C@H:37]4[O:36][CH2:35]3)=[N:22][C:7]2=[N:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 90067176HCID 90067176, compound

Product 1

HCID 131735094HCID 131735094, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (3.1 mg, 0.082 mmol) was added to a stirred solution of 2-[[(3R,3aR,6R,6aR)-6-[6-chloro-5-(4-phenylphenyl)-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]oxy]acetaldehyde (11.1 mg, 0.018 mmol) in MeOH (0.3 ml) that had been cooled to 0° C. in an ice bath. After 1.5 hours, the reaction mixture was removed from the ice bath and allowed to warm to room temperature. The reaction mixture was evaporated under reduced pressure to give the desired product as a white residue. LC-MS: calculated for C32H38ClN3O6Si 623.22 observed m/e: 624.37 (M+H)+ (Rt 1.35/2 min)

Workup

  1. customthe reaction mixture was removed from the ice bath
  2. temperatureto warm to room temperature
  3. customThe reaction mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-72841ae5736e41eabcba1d4c3b2c8955
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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