Sodium borohydride → Benzyl 1-(bicyclo[2.2.2]octan-1-yl)-3-hydroxypropan-2-ylcarbamate

HRID 451796Notes

Reaction equation

HRID 451796 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:17][C:18]12[CH2:25][CH2:24][CH:21]([CH2:22][CH2:23]1)[CH2:20][CH2:19]2)[C:13](OC)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].OS([O-])=O.[Na+]>CO>[C:18]12([CH2:17][CH:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13][OH:14])[CH2:19][CH2:20][CH:21]([CH2:22][CH2:23]1)[CH2:24][CH2:25]2

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 23665763Sodium Bisulfite2×HCID 59201604Methyl 2-(benzyloxycarbonylamino)-3-(bicyclo[2.2.2]octan-1-yl)propanoate

Product 1

HCID 59201578Benzyl 1-(bicyclo[2.2.2]octan-1-yl)-3-hydroxypropan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

methyl 2-(benzyloxycarbonylamino)-3-(bicyclo[2.2.2]octan-1-yl)propanoate (720 mg, 2.087 mmol, 1 eq.) was dissolved in 15 mL of MeOH. NaBH4 (631 mg, 16.7 mmol, 8 eq.) was added in portions. The mixture was stirred for 1.5 h. Saturated aq; NaHSO3 (20 mL) was added and the pH of the mixture was adjusted to 7-8 with NaHSO3 (s). The mixture was evaporated and extracted with EtOAc (20 mL×5). The organic phase was combined and evaporated to give benzyl 1-(bicyclo[2.2.2]octan-1-yl)-3-hydroxypropan-2-ylcarbamate as oil, which was used in the next step without further purification. MS ESI +ve m/z 318 (M+H).

Workup

  1. customThe mixture was evaporated
  2. extractionextracted with EtOAc (20 mL×5)
  3. customevaporated

Sources & evidence

ORD record
ord-f771d784a1bb409fb8d1aef15cd25096
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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