Sodium borohydride → HCID 24993629, compound

HRID 1991367Notes

Reaction equation

HRID 1991367 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:24][CH2:23][C@H:22]3[C@@H:18]([CH2:19][N:20]([C:25]4[C:26](=[O:31])[CH2:27][C:28](=[O:30])[CH:29]=4)[CH2:21]3)[C@@H:17]2[C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[BH4-].[Na+]>CO>[F:40][C:2]([F:1])([F:39])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:24][CH2:23][C@H:22]3[C@@H:18]([CH2:19][N:20]([C:25]4[CH:26]([OH:31])[CH2:27][C:28](=[O:30])[CH:29]=4)[CH2:21]3)[C@@H:17]2[C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86599802HCID 86599802, compound

Product 1

HCID 24993629HCID 24993629, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared as a mixture of diastereomers from the intermediate of step A according to the procedure of Example 6, step C (NaBH4 in methanol). 1H-NMR (CDCl3): rotamers; δ: 7.71 (1H, s), 7.23 (2H, s), 7.00 (2H, m), 6.93 (2H, t, J=8.2 Hz), 4.88-4.65 (2H, m), 4.46 (1H, m), 4.07 (0.5H, m), 3.83 (0.5H, m), 3.55 (1H, m), 3.35 (1H, m), 3.28 (1H, m), 2.97 (2H, m), 2.92 (1H, m), 2.58 (1H, m), 2.43 (1H, m), 2.25 (1H, m), 2.13 (1H, m), 2.05-1.85 (2H, m), 1.70-1.55 (2H, m), 1.30 (3H, 2d, J=6.0 Hz). MS: (MH)+572.5 The diastereomers were separated by HPLC on CHIRACEL OD column eluting with hexanes/EtOH (85/15) to afford the individual diastereomers.

Workup

  1. customMS: (MH)+572.5 The diastereomers were separated by HPLC on CHIRACEL OD column
  2. washeluting with hexanes/EtOH (85/15)
  3. customto afford the individual diastereomers

Sources & evidence

ORD record
ord-b604bdb8c2984e9e97bff0e57a4ba89c
Source dataset
uspto-grants-2010_01
Patent number
US07645790B2

Reaction notes

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