Tert-butyl 5-chlorospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate → tert-butyl 5-chloro-1-((5R,7R)-5-methyl-7-(4-nitrobenzoyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

HRID 529097Notes

Reaction equation

HRID 529097 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([O:10][C@H:11]2[C:15]3[N:16]=[CH:17][N:18]=[C:19](Cl)[C:14]=3[C@H:13]([CH3:21])[CH2:12]2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:24][C:25]1[CH:26]=[C:27]2[C:33]3([CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34]3)[CH2:32][NH:31][C:28]2=[CH:29][CH:30]=1>>[Cl:24][C:25]1[CH:26]=[C:27]2[C:33]3([CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34]3)[CH2:32][N:31]([C:19]3[C:14]4[C@H:13]([CH3:21])[CH2:12][C@@H:11]([O:10][C:8](=[O:9])[C:7]5[CH:22]=[CH:23][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=5)[C:15]=4[N:16]=[CH:17][N:18]=3)[C:28]2=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 69813251Tert-butyl 5-chlorospiro[indoline-3,3'-pyrrolidine]-1'-carboxylateHCID 86651804(5R,7R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate

Product 1

HCID 69811182tert-butyl 5-chloro-1-((5R,7R)-5-methyl-7-(4-nitrobenzoyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

Procedure

tert-butyl 5-chloro-1-((5R,7R)-5-methyl-7-(4-nitrobenzoyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,3′-pyrrolidine]-1′-carboxylate was prepared by the procedures described in Example 1, Step 8, substituting (R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine with (5R,7R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate, and substituting tert-butyl 5-chlorospiro[indoline-3,4′-piperidine]-1′-carboxylate with tert-butyl 5-chlorospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate. LCMS (APCI+) m/z 339.1 [M+H−Boc-pNO2 benzoic acid]+; Rt=4.74 min.

Sources & evidence

ORD record
ord-aab4b863e27d4fdb8ab53c594725091c
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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