Dimethylformamide → HCID 67355077, compound

HRID 1672385Notes

Reaction equation

HRID 1672385 reaction equation
[CH2:1]([N:8]([CH2:15][C:16]([O:18]C)=[O:17])[CH2:9][C:10]1([CH2:13]I)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.[H-].[Na+]>>[CH2:1]([N:8]1[CH:15]([C:16]([OH:18])=[O:17])[CH2:13][C:10]2([CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 86614566HCID 86614566, compound

Product 1

HCID 67355077HCID 67355077, compound

Procedure

To a stirred solution of methyl (benzyl{[1-(iodomethyl)cyclopropyl]methyl}amino)acetate (0.10 g, 0.00027 mol) in DMF (2.0 mL, 0.026 mol) at RT was added sodium hydride (16 mg, 0.00040 mol). The reaction mixture was stirred at RT for 1 h to achieve the desired cyclization and hydrolysis of the methyl ester. The reaction was quenched by the addition of water and acidified with 1 N HCl to pH 3-4 and washed with EtOAc. The aqueous layer was concentrated in vacuo to afford the desired product as a yellow solid, which was used in the next step without purification. LC/MS: m/e 232.2 (M+1H)+.

Workup

  1. customThe reaction was quenched by the addition of water
  2. washwashed with EtOAc
  3. concentrationThe aqueous layer was concentrated in vacuo

Sources & evidence

ORD record
ord-615bc446f0a64b31bca751ccd779bbeb
Source dataset
uspto-grants-2011_08
Patent number
US07998959B2

Reaction notes

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