Hydrochloric Acid → Tert-butyl 2-fluoro-cyclopropane-1-carboxylate

HRID 130612

반응식

HRID 130612 반응식
[BH4-].[Na+].Cl[C:4]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH:5]1[F:7].O.Cl>CN1C(=O)CCC1.O.O.O.O.O.O.[Co](Cl)Cl.C1(C)C=CC=CC=1>[F:7][CH:5]1[CH2:6][CH:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 11858685Tert-butyl 1-chloro-2-fluoro-cyclopropane-1-carboxylate

생성물 1

HCID 11819326Tert-butyl 2-fluoro-cyclopropane-1-carboxylate수율 98%

시약·촉매·용매 3

HCID 517166Dichlorocobalt hexahydrate촉매HCID 1140Toluene용매HCID 13387N-methyl-2-pyrrolidone용매3회

실험 절차

Sodium borohydride (8.75 g, 231.21 mmol) was dissolved in NMP (95 mL) under stirring with a stirring blade at room temperature. Subsequently, to the resultant solution was added an NMP solution (20 mL) of tert-butyl 1-chloro-2-fluoro-cyclopropane-1-carboxylate (cis/trans=62/38) (hereinafter the compound will be referred to as “compound (1a)”) (30 g, 154.14 mmol). An NMP solution (35 mL) of cobalt chloride hexahydrate (1.1 g, 4.62 mmol) was gradually added to the resultant reaction mixture under ice cooling. After completion of dropwise addition, the resultant mixture was stirred with a stirring blade at room temperature for 30 minutes, and at 40° C. for three hours. After completion of reaction, water (120 mL) was added to the resultant reaction mixture at the same temperature, followed by addition of 5 N hydrochloric acid (30 mL). Subsequently, toluene was added to the reaction mixture for extraction. The resultant toluene layer was washed with water, and then dried over sodium sulfate, to thereby yield a toluene solution containing 24.3 g (yield: 98%) of the title compound. Yield was determined by means of high performance liquid chromatography (HPLC) (the same shall apply hereinafter).

후처리

  1. customreaction mixture under ice cooling
  2. additionAfter completion of dropwise addition
  3. additionwas added to the resultant
  4. customreaction mixture at the same temperature
  5. washThe resultant toluene layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. customto thereby yield a toluene solution

출처 및 근거

ORD 기록
ord-31dde147dee64b16bd0a80d7ce46349c
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381833B2

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