Dichloromethane → Benzyl N-(3-hydroxypropyl)carbamate

HRID 1525944Notes

Reaction equation

HRID 1525944 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].C([O-])([O-])=O.[Na+].[Na+].[CH:12]1[CH:17]=[CH:16][C:15]([CH2:18][O:19][C:20](Cl)=[O:21])=[CH:14][CH:13]=1.C(Cl)Cl>C1COCC1.O>[OH:5][CH2:4][CH2:3][CH2:2][NH:1][C:20](=[O:21])[O:19][CH2:18][C:15]1[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 90863-Amino-1-propanolHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformate

Product 1

HCID 562256Benzyl N-(3-hydroxypropyl)carbamateYield 90.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-aminopropan-1-ol (5.0 g, 67 mmol), Na2CO3 (8.8 g, 83 mmol) in THF (40 mL) and H2O (130 mL) at 0° C. was added Cbz-Cl (14.8 g, 87 mmol). The reaction mixture was stirred (RT, 1 h). Water (500 mL) and CH2Cl2 (500 mL) were added, and the layers were separated. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (PE:EtOAc, 5:1) to afford benzyl 3-hydroxypropylcarbamate as a white solid (12.6 g, 90.5%).

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (PE:EtOAc, 5:1)

Sources & evidence

ORD record
ord-fdb00e7648ad433ea4abde29988d7158
Source dataset
uspto-grants-2015_07
Patent number
US09085527B2

Reaction notes

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