Trifluoroacetic acid → HCID 178484802, compound

HRID 1743763Notes

Reaction equation

HRID 1743763 reaction equation
C(O[C:6](=O)[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]#[C:16][CH2:17][OH:18])[CH2:11][CH2:10]1)C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:6][NH:7][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]#[C:16][CH2:17][OH:18])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178486040HCID 178486040, compound

Product 1

HCID 178484802HCID 178484802, compoundYield 103.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9.0 g (33.66 mmol) of trans-[4-(3-Hydroxy-prop-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 185 ml CH2Cl2 was treated at 0° C. with 136 ml of TFA (for 30 min). After 15 min at this temperature, the reaction was evaporated, treated with cold (0° C.) 1 N NaOH (saturated with NaCl) and extracted with CH2Cl2/MeOH 9:1 (3×). The organic phase was dried over Na2SO4 and evaporated to yield 5.84 g (quantitative) of trans-3-(4-Methylamino-cyclohexyl)-prop-2-yn-1-ol, MS: 167 (M).

Workup

  1. customthe reaction was evaporated
  2. additiontreated with cold (0° C.) 1 N NaOH (saturated with NaCl)
  3. extractionextracted with CH2Cl2/MeOH 9:1 (3×)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-c539e64d69de44cea18034632de92808
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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