p-Toluenesulfonic acid → 2-Bromomethyl-1,4-dioxa-7-azaspiro[4.4]nonane benzyl carbamate

HRID 846694Notes

Reaction equation

[CH2:1]([NH:8][C:9](=[O:11])[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:12]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13]1.[Br:18][CH2:19][CH:20](O)[CH2:21][OH:22].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([NH:8][C:9](=[O:10])[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18][CH2:19][CH:20]1[CH2:21][O:22][C:14]2([CH2:15][CH2:16][NH:12][CH2:13]2)[O:17]1

Participants

Conditions

Temperature: 110 °C

Procedure

A 1.00 g (4.56 mmol) sample of 3-pyrrolidinone benzyl carbamate, from Step 2 Example 1, was dissolved in 20 mL of toluene with 1.00 g (11.4 mmol) of 3-bromo-1,2-propanediol and 0.043 g (0.23 mmol) of p-toluenesulfonic acid and heated at 110° C. for 24 hours. The reaction solution was poured into 20% sodium bicarbonate solution and the mixture extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent removed under vacuum to afford 1.22 g of the title compound as a dark liquid: MS M/Z 356 (M). NMR: d 2.06 (m, 2H), 3.32 (m, 1H), 3.44 (m, 2H), 3.55 (m, 3H), 3.91 (m, 1H), 4.11 (m, 1H), 4.37 (m, 1H), 5.13 (s, 2H), 7.35 (m, 5H).

Workup

extractionthe mixture extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous sodium sulfate
customthe solvent removed under vacuum

Sources & evidence

ORD record: ord-bcc1b921e3044864807df3b30ff8fc8d
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05137892

Reaction notes

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