Sodium borohydride → HCID 86710399, compound

HRID 1398410Notes

Reaction equation

HRID 1398410 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][O:18][CH:19]([CH3:21])[CH3:20])[C:13](OC)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CC(O)C>[OH:14][CH2:13][C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:17][O:18][CH:19]([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57979844HCID 57979844, compound

Product 1

HCID 86710399HCID 86710399, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

(S)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-isopropoxypropanoate (0.02 g, 0.068 mmol) was taken in 2-propanol (4 mL) and then NaBH4 (7.69 mg, 0.203 mmol) was added and the mixture stirred for overnight at 50° C. After cooling to 0° C., the mixture was quenched with 1N HCl and then extracted with diethyl ether (10 mL). The diethyl ether layer was collected and concentrated under reduced pressure to afford (R)-benzyl (1-hydroxy-3 isopropoxypropan-2-yl)carbamate) (14 mg, 0.058 mmol, 86% crude yield) as colorless oil. The product was carried on without further purification. 1H NMR (400 MHz, MeOD) δ 7.31-7.48 (m, 5H), 5.12 (s, 1H), 4.81 (bs, 1H), 3.41-3.91 (m, 6H), 1.12-1.26 (m, 6H).

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe mixture was quenched with 1N HCl
  3. extractionextracted with diethyl ether (10 mL)
  4. customThe diethyl ether layer was collected
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8e904b4f312d48369a588aa2055929dd
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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