TBAF tetrahydrofuran → HCID 178484178, compound

HRID 1254352Notes

Reaction equation

HRID 1254352 reaction equation
[Si]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][C@H:16]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:17][N:18]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH3:19])[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].C1COCC1>O>[OH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][C@H:16]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])[CH2:17][N:18]([C:20]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21])[CH3:19])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 178484179HCID 178484179, compound

Product 1

HCID 178484178HCID 178484178, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

tert-Butyl (S)-1-(trans-4-(t-butyldimethylsilyloxy)cyclohexyl)-3-(N-(benzyloxycarbonyl)-N-methylamino)propan-2-ylcarbamate (18 g, 34 mmol) was treated with 4 M nBu4NF/THF (50 mL) at 50° C. for 6 h. Water (30 mL) was added and the mixture was extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over MgSO4 and evaporated to give crude tert-butyl (S)-1-(trans-4-hydroxycyclohexyl)-3-(N-(benzyloxycarbonyl)-N-methylamino)propan-2-ylcarbamate (9 g, 64%) that was purified by silica chromatography. 1H NMR (CDCl3, 400 MHz) δ 1.41(d, 9 H), 1.65(m, 6 H), 1.95(m, 3 H), 2.98(d, 3 H), 3.10(m, 1 H), 3.52(m, 1 H), 3.90(m, 1 H), 5.13(d, 2 H), 7.33(m, 5 H).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×100 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-7b27bb23b59e45c68758b4a58b85e12f
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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