Carbon tetrabromide → HCID 69067664, compound

HRID 1985726Notes

Reaction equation

HRID 1985726 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH2:22]O)=[C:14]([Br:24])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:45]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH2:22][Br:45])=[C:14]([Br:24])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67238425HCID 67238425, compound

Product 1

HCID 69067664HCID 69067664, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.400 g (4R,9aR)-7-bromo-6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (example 21 step 1) in 5 ml dichloromethane was added at room temperature 0.4 g triphenylphosphine and carbontetrabromide and the mixture was stirred at room temperature for 30 min. The red-orange solution was purified by chromatography on silica gel with heptane:ethyl acetate=1:1. The product fractions were collected and evaporated. The resulting oil (showing crystal seeds) was triturated with hexane. The crystalline solid was collected and dried to constant weight to yield 0.307 g of the title compound (MS: 406.1; 404.2 (M+H+)).

Workup

  1. customThe red-orange solution was purified by chromatography on silica gel with heptane
  2. customThe product fractions were collected
  3. customevaporated
  4. customThe resulting oil (showing crystal seeds) was triturated with hexane
  5. customThe crystalline solid was collected
  6. customdried to constant weight

Sources & evidence

ORD record
ord-9bddf393eae24807be5d9146e63e5a75
Source dataset
uspto-grants-2009_06
Patent number
US07547699B2

Reaction notes

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