Dichloromethane → cyclopropyl-(R)-pyrrolidin-2-yl-methanol

HRID 926382Notes

Reaction equation

HRID 926382 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH:13]=[O:14])=O)(C)(C)C.[CH:15]1([Mg]Cl)[CH2:17][CH2:16]1.C(=O)([O-])O.[Na+].ClCCl>O1CCCC1>[CH:15]1([C@H:13]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)[OH:14])[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 7009153N-(tert-Butoxycarbonyl)-D-prolinalHCID 178478986HCID 178478986, compound

Product 1

HCID 89726206cyclopropyl-(R)-pyrrolidin-2-yl-methanolYield 14.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (200 mg, 1 mmol) in tetrahydrofuran at −78° C. was added a 1 M solution of cyclopropylmagnesium chloride (1.3 ml, 1.3 mmol). After stirring for 1 h at room temperature and addition of aqueous sodium hydrogencarbonate, extraction (3 times with dichloromethane), drying of the combined organic layers over sodium sulfate and evaporation of the solvents the crude product was heated with aqueous sodium hydroxide at 100° C. for 3 days to give 20 mg of crude cyclopropyl-(R)-pyrrolidin-2-yl-methanol which was used in the next step without further purification.

Workup

  1. dry with materialdrying of the combined organic layers over sodium sulfate and evaporation of the solvents the crude product
  2. temperaturewas heated with aqueous sodium hydroxide at 100° C. for 3 days

Sources & evidence

ORD record
ord-b3a64f72b9c64a8f830c6fa0cd48e8b3
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

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