Nitrogen → HCID 178523768, compound

HRID 1044801Notes

Reaction equation

HRID 1044801 reaction equation
N#N.[CH2:3]([O:10][C:11]([NH:13][C@@H:14]1[CH2:19][CH2:18][C@H:17]([C:20](O)=[O:21])[CH2:16][CH2:15]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S(C)C.[BH4-].[Na+]>C1COCC1.CO>[CH2:3]([O:10][C:11]([NH:13][C@@H:14]1[CH2:19][CH2:18][C@H:17]([CH2:20][OH:21])[CH2:16][CH2:15]1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 1068Dimethyl Sulfide2×HCID 4311764Sodium borohydrideHCID 178523780HCID 178523780, compound

Product 1

HCID 178523768HCID 178523768, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of cis-4-benzyloxycarbonylaminocyclohexanecarboxylic acid (417 mg, 1.50 mmol) in THF (15 mL) was added BH3.Me2S complex (2.0 M in THF, 1.5 mL, 3.00 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h30. More BH3.Me2S complex (2.0 M in THF, 1.0 mL, 2.00 mmol) was added at 0° C. followed by NaBH4 (12 mg, 0.30 mmol). The reaction mixture was warmed to rt and stirred at this temperature until completion of the reaction. MeOH was carefully added to quench the reaction, the volatiles were removed under reduced pressure and the residue co-evaporated with MeOH (2×). Purification by FC (hept-EA, 1:0->3:2) gave pure cis-4-benzyloxycarbonylaminocyclohexane-methanol as a colorless oil. TLC:rf (1:2 hept-EA)=0.45. LC-MS-conditions 01: tR=0.82 min; [M+H]+=264.07.

Workup

  1. additionwas added BH3
  2. customat 0° C
  3. temperatureThe reaction mixture was warmed to rt
  4. stirringstirred at this temperature until completion of the reaction
  5. customto quench
  6. customthe reaction
  7. customthe volatiles were removed under reduced pressure
  8. customPurification by FC (hept-EA, 1:0->3:2)

Sources & evidence

ORD record
ord-e8355445806a46a3ac33fcf739cb36d2
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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