1-Bromopentane → HCID 67357239, compound

HRID 2385325Notes

Reaction equation

HRID 2385325 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([C:21]3[C:12](=[CH:13][C:14]4OCC[O:16][C:15]=4[CH:20]=3)[O:11][CH2:10]2)[C:2]1=[O:22].N1C2[C:26](=[CH:27]C=CC=2)[C@@:25]2(C3[C:34](=CC4OCCOC=4C=3)[O:33][CH2:32]2)C1=O.BrCCC[CH2:49][O:50][CH3:51].BrCCCCC>>[CH3:34][O:33][CH2:32][CH2:25][CH2:26][CH2:27][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([C:21]3[C:12](=[CH:13][C:14]4[CH2:51][O:50][CH2:49][O:16][C:15]=4[CH:20]=3)[O:11][CH2:10]2)[C:2]1=[O:22]

Participants

5

Reactant 4

HCID 80571-BromopentaneHCID 5211681-Bromo-4-methoxybutaneHCID 58224164Spiro[furo[2,3-g]-1,4-benzodioxin-8(7H),3'-[3H]indol]-2'(1'H)-one, 2,3-dihydroHCID 59352191Spiro[furo[2,3-g]-1,4-benzodioxin-8(7H),3'-[3H]indol]-2'(1'H)-one, 2,3-dihydro-, (3'S)-

Product 1

HCID 67357239HCID 67357239, compound

Procedure

Following the procedure as described in EXAMPLE 7.3 and making non-critical variations using 2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one to replace (S)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one, and 1-bromo-4-methoxybutane to replace 1-bromopentane, 1′-(4-methoxybutyl)-2,3-dihydrospiro[furo[2,3-g][1,3]benzodioxine-8,3′-indol]-2′(1′H)-one was obtained (93%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.30-6.86 (m, 4H), 6.45 (s, 1H), 6.18 (s, 1H), 4.72 (ABq, 2H), 4.18-4.04 (m, 4H), 3.88-3.63 (m, 2H), 3.44-3.37 (m, 2H), 3.30 (s, 3H), 1.88-1.56 (m, 4H); 13C NMR (75 MHz, CDCl3) δ177.2, 155.2, 144.5, 142.3, 138.2, 132.5, 128.8, 123.9, 123.1, 121.1, 111.4, 108.6, 99.3, 80.1, 72.0, 64.5, 63.9, 58.6, 57.9, 40.0, 26.9, 24.3; MS (ES+) m/z 381.9 (M+1).

Sources & evidence

ORD record
ord-30e22882016b4c4590fe7b0a49a32a7a
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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