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

HRID 471232Notes

Reaction equation

HRID 471232 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-64eaaa419a9849fab2271ef6da8ed468
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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