5-Nitroindoline → HCID 86671002, compound

HRID 515381Notes

Reaction equation

HRID 515381 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7]2)([O-:3])=[O:2].O=[C:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.[Na]>C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)[CH2:8][CH2:7]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 362195-NitroindolineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5360545Sodium

Product 1

HCID 86671002HCID 86671002, compoundYield 122.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Nitroindoline (12.18 mmol, 2 g) was stirred in acetic acid (50 mL) in an ice bath. tert-Butyl 4-oxopiperidine-1-carboxylate (14.62 mmol, 2.91 g) was added, followed by the portionwise addition of sodium triacetoxyhydroborate (18.27 mmol, 3.87 g). The reaction mixture was stirred for 1 hour at room temperature. The reaction mixture was concentrated at reduced pressure. The resulting residue was taken up in ethyl acetate and washed with saturated sodium bicarbonate solution. The organic phase was concentrated at reduced pressure to afford the title compound (5.2 g).

Workup

  1. concentrationThe reaction mixture was concentrated at reduced pressure
  2. washwashed with saturated sodium bicarbonate solution
  3. concentrationThe organic phase was concentrated at reduced pressure

Sources & evidence

ORD record
ord-eba63af6ad8448449efa8d717f9ce57b
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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