Diisopropylethylamine → HCID 66661400, compound

HRID 2275524Notes

Reaction equation

HRID 2275524 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH:14]1[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([N:14]3[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15]3)=[O:13])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 986061-(p-Chlorophenyl)cyclopropanecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2733874(3S)-pyrrolidin-3-ol

Product 1

HCID 66661400HCID 66661400, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-chlorophenyl)cyclopropanecarboxylic acid (50 mg, 0.25 mmol), (3S)-pyrrolidin-3-ol (24.4 mg, 0.28 mmol) and BOP (116.0 mg, 0.26 mmol) in 0.4 mL DMF was added hunig base (0.066 ml, 0.38 mmol). The mixture was stirred at room temperature overnight and directly purified by prep. HPLC to provide (3S)-1-((1-(4-chlorophenyl)cyclopropyl)carbonyl)pyrrolidin-3-ol (20 mg). LCMS: m/z 266.0 (M+H)+; 553.1 (2M+Na)+.

Workup

  1. customdirectly purified by prep

Sources & evidence

ORD record
ord-eb31345d4493445b92d4baf2042c2af6
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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