Triphosgene → (S)-3-isocyanato-2,2-dimethyl-butane

HRID 403572

Reaction equation

HRID 403572 reaction equation
[CH3:1][C@H:2]([NH2:7])[C:3]([CH3:6])([CH3:5])[CH3:4].[C:8]([O-])(O)=[O:9].[Na+].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[N:7]([C@@H:2]([CH3:1])[C:3]([CH3:6])([CH3:5])[CH3:4])=[C:8]=[O:9]

Participants

5

Reactant 3

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 7004913(2S)-3,3-dimethylbutan-2-amine

Product 1

HCID 12169316(S)-3-isocyanato-2,2-dimethyl-butaneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-1,2,2-trimethylpropylamine (626 mg, 6.2 mmol) in methylene chloride (20 mL) and satd aq NaHCO3 (20 mL) was added triphosgene (607 mg, 2.05 mmol) at 0° C. The mixture was stirred for 15 min. The organic phase was separated, dried and concentrated to give (S)-3-isocyanato-2,2-dimethyl-butane (845 mg, 90%). 1H NMR (CDCl3): 0.90 (s, 9H), 1.21 (m, 3H), 3.31 (m, 1H).

Workup

  1. customThe organic phase was separated
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-28eb4bf7a3314f19b7230cd5ea3248b3
Source dataset
uspto-grants-2014_06
Patent number
US08748444B2

Linked notes

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