Hydrochloric Acid → HCID 86696715, compound

HRID 2365860Notes

Reaction equation

HRID 2365860 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[CH:9]2[CH2:10][CH:6]([CH2:7][CH:8]2[NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:5]1.[Cl-].[Cl-].[Ca+2].Cl>C(O)C>[OH:5][CH:6]1[CH2:7][CH:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]([CH2:4][OH:3])[CH2:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 86696714HCID 86696714, compound

Product 1

HCID 86696715HCID 86696715, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 (0.580 g, 15.2 mmol) was added to a solution of benzyl 3-oxo-2-oxa-bicyclo[2.2.1]heptan-5-ylcarbamate (1.0 g, 3.8 mmol) and CaCl2 (0.85 g, 7.6 mmol) in ethanol (50 mL) at 0° C. After being stirred at room temperature for 12 hours, the reaction mixture was treated with concentrated HCl. The volatiles were removed, and the residue was extracted with CHCl3 (3×100 mL), washed with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated. The residue was re-crystallized from petroleum ether to afford benzyl 4-hydroxy-2-(hydroxymethyl)cyclopentylcarbamate (750 mg, 75% yield) as a solid. 1H NMR (500 MHz, (CD3)2SO) δ 7.38-7.31 (m, 5H), 7.25 (d, J=13.5 Hz, 1H), 4.99 (s, 2H), 4.53 (d, J=4 Hz, 1H), 4.48 (t, J=10 Hz, 1H), 4.09 (d, J=4 Hz, 1H), 3.73 (t, J=15.5 Hz, 1H), 3.46-3.43 (m, 1H), 3.31-3.28 (m, 1H), 1.99 (d, J=7 Hz, 1H), 1.80-1.74 (m, 2H), 1.57 (t, J=12.5 Hz, 1H), 1.26 (s, 1H).

Workup

  1. customThe volatiles were removed
  2. extractionthe residue was extracted with CHCl3 (3×100 mL)
  3. washwashed with water (50 mL) and brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was re-crystallized from petroleum ether

Sources & evidence

ORD record
ord-d831efad6ef0443a8fa80e7c82339c9e
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

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