Acetic Acid → HCID 178523790, compound

HRID 1963949Notes

Reaction equation

HRID 1963949 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][CH2:3]1.[O:19]1[CH2:23][CH2:22][C:21](=O)[CH2:20]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[O:19]1[CH2:23][CH2:22][CH:21]([NH:1][C@H:2]2[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:4][CH2:3]2)[CH2:20]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5293923-OxotetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 178511686HCID 178511686, compound

Product 1

HCID 178523790HCID 178523790, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of benzyl trans-4-aminocyclohexylcarbamate (396 mg, 1.595 mmol) in CH2Cl2 (9 ml) was added dihydrofuran-3(2H)-one (151 mg, 1.754 mmol) followed by acetic acid (150 μL, 2.62 mmol) and sodium triacetoxyborohydride (439 mg, 2.073 mmol) under Argon. Stirred at 25° C. for 16 h, then concentrated in vacuo. The resulting residue was partitioned between EtOAc and 1M NaOH. The organics were combined, then washed with 1M NaOH (×2), water (×2), saturated brine (×2), then dried (Na2SO4), filtered and evaporated under reduced pressure to give racemic benzyl trans-4-(tetrahydrofuran-3-yl-amino)cyclohexylcarbamate (495 mg). The resulting residue was used in next step without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was partitioned between EtOAc and 1M NaOH
  3. washwashed with 1M NaOH (×2), water (×2), saturated brine (×2)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-72a263faef264266ad5eac72508da5b5
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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