Toluene → 2,2,2-Trifluoro-1-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone trifluoroacetate

HRID 1689462Notes

Reaction equation

HRID 1689462 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:31])([F:30])[C:10]([N:12]1[CH2:17][C:16]2([CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)[O:15][CH2:14][CH2:13]1)=[O:11].C1(C)C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:31][C:9]([F:8])([F:30])[C:10]([N:12]1[CH2:17][C:16]2([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[O:15][CH2:14][CH2:13]1)=[O:11]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57989171Tert-butyl 4-(2,2,2-trifluoroacetyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 866367502,2,2-Trifluoro-1-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (66 mL) was added to a solution of tert-butyl 4-(2,2,2-trifluoroacetyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (example 101, step d) (4.33 g) in DCM (66 mL) and the resulting mixture was stirred at RT for 20 min. Toluene (50 mL) was added and the mixture was evaporated in vacuo (×3) to give the subtitled compound. Yield 5.52 g.

Workup

  1. customthe mixture was evaporated in vacuo (×3)

Sources & evidence

ORD record
ord-05a8c400409246c39443b0fd9f5d8d2c
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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