Acetic Acid → HCID 90416975, compound

HRID 633587Notes

Reaction equation

HRID 633587 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[C:13]1[C:21]2[C:16](=[C:17]([O:22][CH3:23])[N:18]=[CH:19][CH:20]=2)[N:15]([CH3:24])[CH:14]=1.[NH:30]1[CH2:35][CH2:34][CH:33]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:32][CH2:31]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][N:30]2[CH2:31][CH2:32][CH:33]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:41])([CH3:40])[CH3:42])[CH2:34][CH2:35]2)=[CH:7][C:6]=1[C:13]1[C:21]2[C:16](=[C:17]([O:22][CH3:23])[N:18]=[CH:19][CH:20]=2)[N:15]([CH3:24])[CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 90417507HCID 90417507, compound

Product 1

HCID 90416975HCID 90416975, compoundYield 426.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 105B (125 mg, 0.317 mmol), tert-butyl piperidin-4-ylcarbamate (190 mg, 0.951 mmol) and acetic acid (0.181 mL, 3.17 mmol) in dichloromethane (3 mL) was heated at 50° C. for 1 hour. The reaction mixture was cooled in an ice bath and the sodium triacetoxyborohydride (134 mg, 0.634 mmol) was added portionwise over a few minutes. The reaction mixture was stirred 2 hours while warming to ambient temperature. The reaction mixture was quenched with 1 M sodium hydroxide (2 mL) and partitioned between saturated aqueous sodium bicarbonate solution (50 mL) and ethyl acetate (50 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to provide the title compound (783 mg, 100% yield).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. customThe reaction mixture was quenched with 1 M sodium hydroxide (2 mL)
  3. custompartitioned between saturated aqueous sodium bicarbonate solution (50 mL) and ethyl acetate (50 mL)
  4. customThe layers were separated
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f03582aa94a64c2a96aeec4ec5fe7fcc
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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