Carbamic Acid → HCID 78035674, compound

HRID 1422600Notes

Reaction equation

HRID 1422600 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]23[CH2:16][CH:15]2[CH2:14][O:13]C(=O)N3)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].O.[OH-].[Li+].[C:21](=[O:24])([OH:23])[NH2:22].Cl.[C:26](=O)=O.[OH-].[Na+]>O.C(O)C>[OH:13][CH2:14][CH:15]1[CH2:16][C:10]1([NH:22][C:21](=[O:23])[O:24][CH3:26])[C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

9

Reactant 6

HCID 277Carbamic AcidHCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 71184136HCID 71184136, compound

Product 1

HCID 78035674HCID 78035674, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Step a) A mixture of (1SR,6RS)-1-(3-nitrophenyl)-4-oxa-2-azabicyclo[4.1.0]heptan-3-one (3.55 g, 15.2 mmol, Eq: 1.00) and lithium hydroxide monohydrate (6.36 g, 152 mmol, Eq: 10) in water (40 ml) and ethanol (8 ml) was stirred at 100° C. for 1.75 h. Cooled to 23° C., huge precipitate (salt of the carbamic acid), acidified with conc. HCl to pH<1 (CO2 evolution!), stirred at 23° C. for 5 min, made alkaline with 10 M NaOH-sol., extracted thrice with dichloromethane, dried combined organic layer over Na2SO4. Removal of the solvent in vacuum left the ((1RS,2SR)-2-amino-2-(3-nitrophenyl)cyclopropyl)methanol (3.085 g, 14.8 mmol, 97.8% yield) as a brown oil.

Workup

  1. temperatureCooled to 23° C.
  2. stirringstirred at 23° C. for 5 min
  3. extraction, extracted thrice with dichloromethane
  4. customdried
  5. customRemoval of the solvent in vacuum

Sources & evidence

ORD record
ord-0ccdb5a03bbc41a08c435da06d7ab566
Source dataset
uspto-grants-2015_01
Patent number
US08927535B2

Reaction notes

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