N-bromobutanimide → HCID 70654455, compound

HRID 2403652Notes

Reaction equation

HRID 2403652 reaction equation
[C:1]([N:5]1[CH:28]=[C:27]2[C:7]([CH:8]=[CH:9][C:10]3([CH2:26]2)[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:12][CH2:11]3)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[Br:29]N1C(=O)CCC1=O.CO.[O:39]1[CH2:43]CCC1>>[Br:29][CH:9]1[C:10]2([CH2:11][CH2:12][N:13]([C:16]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:17])[CH2:14][CH2:15]2)[CH2:26][C:27]2[C:7](=[N:6][N:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:28]=2)[CH:8]1[O:39][CH3:43]

Participants

4

Reactant 3

HCID 67184N-bromobutanimideHCID 21899815MeOH tetrahydrofuranHCID 57337173HCID 57337173, compound

Product 1

HCID 70654455HCID 70654455, compoundYield 73%

Procedure

Benzyl 2-tert-butyl-2,4-dihydrospiro[indazole-5,4′-piperidine]-1′-carboxylate (560 mg, 1.48 mmol) was dissolved in a 20% methanol/tetrahydrofuran mixture (25 mL). N-bromosuccinimide (315 mg, 1.77 mmol) was added and the mixture was stirred for 30 minutes. The mixture was concentrated under reduced pressure. The resultant oil was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic phase was dried over sodium sulfate, filtered and concentrated. The resultant oil was purified by flash column chromatography (10-80% ethyl acetate/heptane) to yield 538 mg (73%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3, δ): 7.27-7.43 (m, 6 H), 5.12 (s, 2 H), 4.74 (d, J=2.7 Hz, 1 H), 4.41 (d, J=2.5 Hz, 1 H), 3.60-3.84 (m, 2 H), 3.54-3.61 (m, 3 H), 3.14-3.39 (m, 2 H), 2.59 (s, 2 H), 1.86 (br. s., 1 H), 1.69 (br. s., 3 H), 1.51-1.60 (m, 9 H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe resultant oil was partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant oil was purified by flash column chromatography (10-80% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-55e1e2d9c6704d3aa40704350f46016d
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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