Potassium Hydroxide → 6-(pyrrolidine-1-carbonyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid

HRID 926356Notes

Reaction equation

HRID 926356 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:15]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[N:9]2[CH2:14][CH2:13][O:12][CH2:11][C:10]=12)=[O:5])C.[OH-].[K+]>O>[N:17]1([C:15]([C:8]2[N:9]3[C:10]([CH2:11][O:12][CH2:13][CH2:14]3)=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=2)=[O:16])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 897267156-(pyrrolidine-1-carbonyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ethyl ester

Product 1

HCID 897268566-(pyrrolidine-1-carbonyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-(pyrrolidine-1-carbonyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ethyl ester (Comp. No. 6a) (0.95 g, 3.25 mmol) and potassium hydroxide (0.91 g, 16.3 mmol) in water (33 ml) was stirred at 100° C. until complete conversion according to LC/MS (ca. 1 h). Approximately half of the solvents were evaporated in vacuo and the mixture was acidified with excess hydrochloric acid. The forming precipitate was filtered off, washed once with water and dried in vacuo to give 0.76 g (88%) of 6-(pyrrolidine-1-carbonyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid as white solid. LC/MS (method 4): Rt=0.92 min; m/z=265.17 (M+H+).

Workup

  1. customaccording to LC/MS (ca. 1 h)
  2. customApproximately half of the solvents were evaporated in vacuo
  3. filtrationThe forming precipitate was filtered off
  4. washwashed once with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-6e7eff9483b941da87268e1fa448e6ce
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

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