Hydrochloric Acid → HCID 68556132, compound

HRID 2370303Notes

Reaction equation

HRID 2370303 reaction equation
[CH2:1]([O:8][C:9](=[O:21])[NH:10][CH:11]1[CH2:18][CH2:17][CH:16]2[CH2:19][CH:12]1[CH2:13][CH2:14][C:15]2=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.Cl>C1COCC1>[CH2:1]([O:8][C:9](=[O:21])[NH:10][CH:11]1[CH2:18][CH2:17][CH:16]2[CH2:19][CH:12]1[CH2:13][CH2:14][CH:15]2[OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 68555825HCID 68555825, compound

Product 1

HCID 68556132HCID 68556132, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

780 mg of (6-Oxo-bicyclo[3.3.1]non-2-yl)-carbamic acid benzyl ester (100) were dissolved in 14 mL of THF under argon, cooled to 0° C. and 113 mg of sodium borohydride were added. The mixture was stirred for 2 h at 0° C., water was added and the pH of solution was adjusted to 2 by addition of 2M HCl. The aqueous layer was extracted with ethyl acetate three times. The combined organic layer was dried over sodium sulfate and evaporated to dryness to give 0.72 g of the desired product. Rt=1.23 min (Method C). Detected mass: 290.3 (M+H+).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate three times
  2. dry with materialThe combined organic layer was dried over sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-f10dac6bbf384b128ec286d3d1ad8e45
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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