Tetrabutylammonium Fluoride → HCID 86760284, compound

HRID 1245625Notes

Reaction equation

HRID 1245625 reaction equation
[Si]([O:8][CH2:9][C@@H:10]1[C@@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH2:13][N:12]([CH2:22][C:23]2([C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:11]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH2:9][C@@H:10]1[C@@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH2:13][N:12]([CH2:22][C:23]2([C:29]([O:31][CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:11]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131726001HCID 131726001, compound

Product 1

HCID 86760284HCID 86760284, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8.1 g (15.0 mmol) 1-{[(3R,4S)-3-(tert-butyldimethylsilyloxymethyl)-4-(3-fluorophenyl)pyrrolidin-1-yl]methyl}cyclohexanecarboxylic acid, benzyl ester (from Step A) in 150 mL of THF at 0° C. was treated with 45 mL of 1.0 M tetrabutylammonium fluoride solution in THF. The resulting mixture was warmed to rt and stirred for 20 h. The reaction mixture was partitioned between 200 mL of ether and 100 mL of 50% sat'd NaHCO3 and the layers were separated. The organic layer was dried over MgSO4 and concentrated. Purification by Biotage Flash 40 using a 40 M cartridge and 0.5 L to 1.0 L of 9:1 to 2:1 v/v hexane/ethyl acetate as the eluant afforded the title compound: 1H NMR (500 MHz, CDCl3) δ 1.23–3.68 (20H), 5.18 (ABq, J=12.3, 2H), 6.88–7.01 (3H), 7.21–7.40 (6H).

Workup

  1. customThe reaction mixture was partitioned between 200 mL of ether and 100 mL of 50%
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customPurification by Biotage Flash 40 using a 40 M cartridge and 0.5 L to 1.0 L of 9:1 to 2:1 v/v hexane/ethyl acetate as the eluant

Sources & evidence

ORD record
ord-a7beb41d449345eea49703edf77f05ee
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

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